Skip to main content
SpringerLink
Log in
Book cover

Organoselenium Chemistry pp 143–176Cite as

Selenium at Higher Oxidation State

  • Chapter
  • First Online:

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 208))

Abstract

Until recently, selenium derivatives at a higher oxidation state had found rather limited use in organic synthesis. The last ten years, however, have shown that these species are valuable reagents and intermediates which allow clean and high-yielding transformations of a variety of functional groups even in very complex structures in a chemo- regio- and stereoselective manner, under rather mild reaction conditions. A comprehensive review of the synthetic utility of these compounds is presented here with particular emphasis on the stereochemical aspects of their use as reagents.

This is a preview of subscription content, log in via an institution.

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   259.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   329.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD   329.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

8 References

  1. Paquette LA (ed) (1995) Encyclopedia of reagents for organic synthesis. Wiley, Chichester

    Google Scholar 

  2. For some books on organoselenium reagents, see (a) Patai S, Rappoport Z (eds) (1986) The chemistry of organic selenium and tellurium compounds. Wiley, Chichester; (b) Paulmier C (1986) Selenium reagents and intermediates in organic synthesis. Pergamon, Oxford; (c) Liotta D (ed) (1987) Organoselenium chemistry.Wiley, Chichester; (d) Krief A, Havesi L (1988) Organoselenium chemistry. Springer, Berlin Heidelberg New York

    Google Scholar 

  3. For some reviews on organoselenium reagents, see (a) Sharpless KB, Verhoven TR (1979) Aldrichim Acta 12:63; (b) Clive DL (1978) Tetrahedron 34:1049; (c) Reich HJ (1979) Acc Chem Res 12:22; (d) Nicolaou KC, Petasis NA (1984) Selenium in natural products synthesis. CSI, Philadelphia; (e) Rabjohn N (1976) Org React 24:261

    CAS  Google Scholar 

  4. Drabowicz J, Mikołajczyk M (1998) The Fifth International Conference on Heteroatom Chemistry, London (Ontario), Canada

    Google Scholar 

  5. (a) Toshimitsu A, Nakano A, Mukai T, Tamao K (1996) J Am Chem Soc 118:2756; (b) Wirth T (1995) Angew Chem Int Ed Engl 34:1726; (c) Fujita K, Murata K, Iwaoka M, Tomoda S (1995) J Chem Soc Chem Commun 1641; (d) Deziel R, Malenfant E (1995) J Org Chem 60:4660; (e) Lipshutz BH, Gross TJ (1995) J Org Chem 60:3572; (f) Fukuzawa S, Kasugara Y, Uemura S (1994) Tetrahedron Lett 35:9403; (g) Deziel R, Goulet S, Grenier L, Bordeleau J, Berner J (1993) J Org Chem 58:3619; (h) Tiecco M, Testaferri L, Tingoli M, Bagnoli L, Santi C (1993) J Chem Soc Chem Commun 637; (i) Kang SH, Lee SB (1993) Tetrahedron Lett 34:1955; (j) Mihelich ED, Hite GA (1992) J. Am Chem Soc 114:7318; (k) Lipshutz BH, Barton CJ (1992) J Am Chem Soc 114:1084; (l) Mihelich ED (1990) J Am Chem Soc 112 8995

    Article  CAS  Google Scholar 

  6. Yamauchi K, Nakamura K, Kinoshita M (1979) Tetrahedron Lett 1787

    Google Scholar 

  7. Uenemoto T, Ishihara S (1993) J Am Chem Soc 115:2156

    Article  Google Scholar 

  8. Kevill DN, Anderson SW (1991) J Org Chem 56:1845

    Article  CAS  Google Scholar 

  9. Hashmal JA, Horak V, Khoo LE, Quicksal CO, Sun MK (1981) J Am Chem Soc 103:289

    Article  Google Scholar 

  10. Gosselck J, Peress L, Schenk H, Schmidt G (1965) Angew Chem 77:1440

    Google Scholar 

  11. (a) Kataoka T, Banno Y, Watanabe S, Iwamura S, Shimizu H (1997) Terahedron Lett 38:1809; (b) Kataoka T, Watanabe S, Nara S (1998) Phosphorus Sulfur Silicon 136–138:497

    Article  CAS  Google Scholar 

  12. Markovski LN, Tostienko WI, Marschniuk IG, Paschinnik WI, Shermolovich YG, Iksanova SW (1990) Zhur Org Khim 26:1372

    Google Scholar 

  13. (a) Kondo S, Shibata H, Kunisada H, Yuki Y (1992) Bull Soc Chem Jpn 65:2555; (b) Kondo S Shibata A, Ando T, Kunisada H, Yuki Y (1994) Macromol Rapid Commun 15:291

    Article  CAS  Google Scholar 

  14. Hudlicky M (1990) Oxidation in organic chemistry. ACS, Washington, DC

    Google Scholar 

  15. Fieser M, Fieser L (1965–1995) Reagents for organic synthesis. Wiley, Chichester, vols 1, 2, 3–6, 8, 9, 13, 17

    Google Scholar 

  16. Achremowicz L (1996) Synth Commun 26:1681

    Article  CAS  Google Scholar 

  17. Kuronen P, Laitalainen T, Orma O (1993) J Heterocycl Chem 30:961

    CAS  Google Scholar 

  18. Bulman Page PC, McCarthy TJ (1991) In: Trost BM, Fleming I (eds) Comprehensive organic synthesis. Pergamon, Oxford, vol 7, p 83 and references cited therein

    Google Scholar 

  19. Madec A, Férézou JP (1996) Synlett 867

    Google Scholar 

  20. Shibuya K (1994) Synth Commun 24:2923

    Article  CAS  Google Scholar 

  21. Tsukamoto Y, Sato K, Kinato T, Yani T (1992) Bull Chem Soc Jpn 65:3300

    Article  CAS  Google Scholar 

  22. (a) Kiegiel J, Wovkulich PM, Uskokoviæ MR (1991) Tetrahedron Lett 32:6057; (b) Andrews DR, Barton DHR, Cheng KP, Finet JP, Hesse RH, Johnson G, Pechet MM (1986) J Org Chem 51:163

    Article  CAS  Google Scholar 

  23. Kalsi PS, Chhabra BR, Singh J, Vig R (1992) Synlett 425

    Google Scholar 

  24. (a) Młochowski J (1998) Phosphorus Sulfur Silicon 136–138:191; (b) Młochowski J (1998) Chem Papers 52:45; (c) Guzman JA, Mendoza V, Garcia E, Garibay CF, Olivarez LŻ Maldonado LA (1995) Synth Commun 25:2121; (d) Bir CW, Cooper R (1993) Org Prep Proc Int 25:273; (e) Said SB, Skarzewski J, Młochowski J (1989) Synthesis 223; (f) Payne GB, Smith CW (1957) J Org Chem 22:1680

    Article  Google Scholar 

  25. (a) Drabowicz J, Mikołajczyk M (1978) Synthesis 758; (b) Drabowicz J, Łyżwa P, Mikołajczyk M (1983) Phosphorus Sulfur 17:169; (c) Kudzin ZH, Andrijewski G, Drabowicz J (1994) Heteroatom Chem 5:1

    Google Scholar 

  26. Naota T, Sasao S, Tanaka K, Yamamoto H, Murahashi SI (1993) Tetrahedron Lett 34:4843

    Article  CAS  Google Scholar 

  27. Marcantoni E, Petrini M, Palimanti O (1995) Tetrahedron Lett 36:3561

    Article  CAS  Google Scholar 

  28. (a) Astin S, de Moulds V, Retley HL (1935) J Chem Soc 901; (b) Schaefer JP (1962) J Am Chem Soc 84:713

    Google Scholar 

  29. Lee JG, Kim KC (1992) Tetrahedron Lett 33:6363

    Article  CAS  Google Scholar 

  30. Haroutounian SA (1995) Synthesis 39

    Google Scholar 

  31. Shafer CM, Molinski TF (1996) J Org Chem 61:2044

    Article  CAS  Google Scholar 

  32. Cox GG, Harwood LM (1994) Tetrahedron Asymmetry 5:1669 and references cited therein

    Article  CAS  Google Scholar 

  33. (a) Zborovski YL, Levon WF, Staniniec WI (1994) Żhur Obsh Khim 64:1567; (b) Lendel WG, Pak WI, Pietrus WW, Kijak MY, Mugalina YW (1990) Khim Gieter Soied 1331

    Google Scholar 

  34. Pitre SV, Reddy MVR, Vankar VB, Madhusudann KP (1997) Synth Commun 27:267

    Article  CAS  Google Scholar 

  35. (a) Mikołajczyk M, Łuczak J (1978) J Org Chem 43:2132; (b) Mikołajczyk M, Łuczak J (1988) Żhur Obsh Khim 58:2024

    Article  Google Scholar 

  36. Syper L, Młochowski J (1984) Synthesis 747

    Google Scholar 

  37. Tamagaki S, Hatanaka I, Kozuka S (1977) Bull Soc Chem Jpn 50:3421

    Article  CAS  Google Scholar 

  38. (a) Marino JP, Schwartz A (1979) Tetrahedron Lett 3253; (b) Abatgoglou AG, Bryant DR (1981) Tetrahedron Lett 22:2051

    Google Scholar 

  39. Ogura F, Yamaguchi H, Otsubo T, Tanaka H (1982) Bull Soc Chem Jpn 55:641

    Article  CAS  Google Scholar 

  40. Hartke K, Wandenbourg HH (1989) Liebig Ann Chem 415

    Google Scholar 

  41. (a) Takahashi T, Nakao N, Koizumi T (1997) Tetrahedron Asymmetry 8:3293; (b) Takahashi T, Nakao N, Koizumi T (1996) Chem Lett 207; (c) Takahashi T, Kurose N, Kawanami S, Arai Y, Koizumi T, Shiro M (1994) J Org Chem 59:3262

    Article  CAS  Google Scholar 

  42. (a) Barton DHR, Magnus PD, Rosenfeld MN (1977) J Chem Soc Chem Commun 301; (b) Barton DHR, Brewster AG, Ley SV (1976) J Chem Soc Chem Commun 985; (c) Barton DHR, Ley SV, Magnus PD, Rosenfeld MN (1977) J Chem Soc Perkin Trans 1 567

    Google Scholar 

  43. Ley SV (1987) In: Liotta D (ed) Organoselenium chemistry. Wiley, Chichester, pp 163–206

    Google Scholar 

  44. Barton DHR, Finet JP (1988) Tetrahedron 44:6397

    Article  CAS  Google Scholar 

  45. Henriksen L (1994) Tetrahedron Lett 35:7057

    Article  CAS  Google Scholar 

  46. (a) Barton DHR (1985) Tetrahedron 41:4359; (b) Ye YH, Barton DHR, Lusinchi X, Millet P (1990) Chin J Chem 274

    Article  CAS  Google Scholar 

  47. Barton DHR, Wang TL (1994) Tetrahedron Lett 35:5149

    Article  CAS  Google Scholar 

  48. Drabowicz J, Łuczak J, Łyzwa P, Mikołajczyk M (1998) Phosphorus Sulfur Silicon 136–138:143

    Article  Google Scholar 

  49. (a) Grieco PA, Yokoyama Y, Gilman S, Nishizama N (1977) J Org Chem 42:2034; (b) Hori T, Sharpless KB (1978) J Org Chem 43:1689; (c) Reich HJ, Chow F (1978) Synthesis 299

    Article  CAS  Google Scholar 

  50. Syper L (1989) Synthesis 167

    Google Scholar 

  51. Kubicz E, Młochowski J, Syper L (1991) J Prakt Chem 333:243

    Article  CAS  Google Scholar 

  52. Said SB, Skarzewski J, Młochowski J (1992) Synth Commun 22:1851

    Article  CAS  Google Scholar 

  53. Said SB, Skarzewski J, Młochowski J (1989) Synthesis 223

    Google Scholar 

  54. (a) Melnikov NN, Rokickaya MS (1937) Żhur Obsh Khim 7:1532; (b) Badesha SS, Monczka P, Smith SD (1983) Can J Chem 61:2199

    CAS  Google Scholar 

  55. Kornblum N, Jones WJ, Anderson GJ (1959) J Am Chem Soc 81:4113

    Article  CAS  Google Scholar 

  56. Drabowicz J unpublished results

    Google Scholar 

  57. Lowe W, Rutjes T (1995) J Heterocycl Chem 32:43

    Article  Google Scholar 

  58. Lowe W, Schmidt R (1995) J Heterocycl Chem 32:271

    Google Scholar 

  59. Ogawa S, Kikuchi T, Sasaki A, Chida SI, Sato R (1994) Tetrahedron Lett 35:5469

    Article  CAS  Google Scholar 

  60. Besenyei G, Németh S, Simándi L (1994) Tetrahedron Lett 35:9609

    Article  CAS  Google Scholar 

  61. Dorta RL, Francisco CG, Freire R, Suarez E (1988) Tetrahedron Lett 29:5429

    Article  CAS  Google Scholar 

  62. Dorta RL, Francisco CG, Suarez E (1994) Tetrahedron Lett 35:2049

    Article  CAS  Google Scholar 

  63. Dorta RL, Francisco CG, Suarez E (1994) Tetrahedron Lett 35:1083

    Article  CAS  Google Scholar 

  64. Kawashima T, Ohno F, Okazaki R (1998) Phosphorus Sulfur Silicon 136–138:501

    Article  Google Scholar 

  65. Kurose N, Takahashi T, Koizumi T (1997) Tetrahedron 53:12115

    Article  CAS  Google Scholar 

  66. Kurose N, Takahashi T, Koizumi T (1996) J Org Chem 61:2932

    Article  CAS  Google Scholar 

  67. Kurose N, Takahashi T, Koizumi T (1997) J Org Chem 62:4562

    Article  CAS  Google Scholar 

  68. (a) Drabowicz J, Łuczak J, Mikołajczyk M (1986) 10th IUPAC Congress on Organic Synthesis, Moscow; (b) Drabowicz J, Łuczak J, Mikołajczyk M (1998) J Org Chem 63:9565; (c) Jones LA, Sumner CE Jr, Franzus B, Huang TTS, Snyder JJ (1978) J Org Chem 43:2811; (d) Garegg PJ, Johansson R, Samuelsson B (1984) Synthesis 168

    Google Scholar 

  69. Akabori S, Takanohashi S (1991) Bull Soc Chem Jpn 64:3482

    Article  CAS  Google Scholar 

  70. Leonard KA, Zhou F, Detty MR (1996) Organometallics 15:4285

    Article  CAS  Google Scholar 

  71. Łuczak J, Drabowicz J, Mikołajczyk M unpublished results

    Google Scholar 

  72. (a) Akabori S, Takanohashi Y (1990) Chem Lett 251; (b) Akabori S, Takanohashi Y (1991) J Chem Soc Perkin Trans 1 479; (c) Akabori S, Takanohashi Y, Aoki S, Sato S (1991) J Chem Soc Perkin Trans 1 3121

    Google Scholar 

  73. Takanohashi Y, Tabata N, Tanase T, Akabori S (1993) J Chem Soc Perkin Trans 1 813

    Article  Google Scholar 

  74. Takanohashi Y, Tabata N, Tanase T, Akabori S (1993) J Organomet Chem 450:103

    Article  CAS  Google Scholar 

  75. Akabori S, Takanohashi Y, Takagi S (1990) Synth Commun 20:3187

    Article  CAS  Google Scholar 

  76. Duclos JF, Outurquin F, Paulmier C (1993) Tetrahedron Lett 34:7417

    Article  CAS  Google Scholar 

  77. Duclos JF, Outurquin F, Paulmier C (1995) Tetrahedron Lett 36:2627

    Article  CAS  Google Scholar 

  78. Mikołajczyk M, Drabowicz J, Kiełbasiñski P (1996) Formation of C-Se or C-Te bonds. In: Helmchen G, Hoffmann RW, Mulzer J, Schaumann E (eds) Houben-Weyl Methods of organic chemistry E21, Thieme, Stuttgart, vol 8

    Google Scholar 

  79. Engman L (1987) J Org Chem 52:4086

    Article  CAS  Google Scholar 

  80. Boikov YA, Bakhmenko VB, Ginak AI (1986) Żhur Org Khim 22:298

    CAS  Google Scholar 

  81. Sthur Hansen N, Henriksen L (1996) Synth Commun 26:3345

    Article  Google Scholar 

  82. Ali H, van Lier JE (1991) Tetrahedron Lett 32:5015

    Article  CAS  Google Scholar 

  83. Houllemare D, Ponthieux S, Outurquin F, Paulmier C (1997) Synthesis 101

    Google Scholar 

  84. (a) Chivers T, Doxsee DD, Fait JF, Parvez M (1993) Inorg Chem 32:2243; (b) Chivers T, Doxsee DD, Fait JF (1989) J Chem Soc Chem Commun 1703

    Article  CAS  Google Scholar 

  85. Yasuike S, Kiharda T, Kurita J, Tsuchiya T (1996) J Chem Soc Chem Commun 2183

    Google Scholar 

  86. (a) Shimizu M, Kuwajima I (1980) J Org Chem 45:4063; (b) Tiecco M, Chianelli D, Testaferri L, Tingoli M, Bartoli D (1986) Tetrahedron 42:4889; (c) Uemura S, Ohe K, Sugita N (1988) J Chem Soc Chem Commun 111; (d) Krief A, Dumont W, DeMehiu AE (1988) Tetrahedron Lett 29:3269; (e) Shimizu M, Ando R, Kuwajima I (1984) J Org Chem 49:1230

    Article  CAS  Google Scholar 

  87. Toshimitsu A, Hirosawa C, Tanimoto S, Uemura S (1992) Tetrahedron Lett 33:4017

    Article  CAS  Google Scholar 

  88. (a) Wu JC, Chattopadhyaya J (1989) Tetrahedron 45:4507; (b) Wu JC, Chattopadhyaya J (1990) Tetrahedron 46:2597; (c) Tong W, Wu JC, Sandstrom A, Chattopadhyaya J (1990) Tetrahedron 46:3037; (d) Tong W, Xi Z, Gioeli C, Chattopadhyaya J (1991) Tetrahedron 47:3431

    Article  CAS  Google Scholar 

  89. Lermontov S.A., Zavorin SI, Bakhtin IV, Zefirov NS, Stang PJ (1995) Phosphorus Sulfur Silicon 102:283

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Organic Sulfur Compounds, Center of Molecular and Macromolecular Studies, Polish Academy of Sciences, 90-363, üódź, Sienkiewicza 112, Poland

    Józef Drabowicz & Marian Mikołajczyk

Authors
  1. Józef Drabowicz
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Marian Mikołajczyk
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Institut für Organische, Chemie Universität Basel, St. Johanns-Ring 19, 4056, Basel, Switzerland

    Thomas Wirth

Rights and permissions

Reprints and permissions

Copyright information

© 2000 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Drabowicz, J., Mikołajczyk, M. (2000). Selenium at Higher Oxidation State. In: Wirth, T. (eds) Organoselenium Chemistry. Topics in Current Chemistry, vol 208. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-48171-0_6

Download citation

  • DOI: https://doi.org/10.1007/3-540-48171-0_6

  • Published:

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-540-66516-8

  • Online ISBN: 978-3-540-48171-3

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation